P. aeruginosa Metabolome Database: Isethionic acid (PAMDB001641)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB001641

Identification

Name:

Isethionic acid

Description:

Isethionic acid (C2H6O4S) is a short chain alkane sulfonate containing hydroxy group, is a water soluble liquid used in the manufacture of mild, biodegradable and high foaming anionic surfactants which provides gentle cleansing and soft skin feel.; A colorless, syrupy, strongly acidic liquid that can form detergents with oleic acid. The Pseudomonas aeruginosa ssuEADCB gene cluster is required for the utilization of alkanesulfonates (such as isethionic acid) as sulfur sources, and is expressed under conditions of sulfate or cysteine starvation.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

(2-Hydroxyethyl)sulfonate
(2-Hydroxyethyl)sulfonic acid
(2-Hydroxyethyl)sulphonate
(2-Hydroxyethyl)sulphonic acid
2-Hydroxy-Ethanesulfonate
2-Hydroxy-Ethanesulfonic acid
2-Hydroxy-Ethanesulphonate
2-Hydroxy-Ethanesulphonic acid
2-Hydroxyethane-1-sulfonate
2-Hydroxyethane-1-sulfonic acid
2-Hydroxyethane-1-sulphonate
2-Hydroxyethane-1-sulphonic acid
2-Hydroxyethanesulfonate
2-Hydroxyethanesulfonic acid
2-Hydroxyethanesulphonate
2-Hydroxyethanesulphonic acid
2-Hydroxyethylsulfonate
2-Hydroxyethylsulfonic acid
2-Hydroxyethylsulphonate
2-Hydroxyethylsulphonic acid
b-Hydroxyethanesulfonate
b-Hydroxyethanesulfonic acid
b-Hydroxyethanesulphonate
b-Hydroxyethanesulphonic acid
Beta-Hydroxyethanesulfonate
Beta-Hydroxyethanesulfonic acid
Beta-Hydroxyethanesulphonate
Beta-Hydroxyethanesulphonic acid
Ethanolsulfonate
Ethanolsulfonic acid
Ethanolsulphonate
Ethanolsulphonic acid
Hydroxyethylsulfonate
Hydroxyethylsulfonic acid
Hydroxyethylsulphonate
Hydroxyethylsulphonic acid
Isethionate
Isethionate sodium salt
Isethionic acid
Isethionic acid sodium salt
Kyselina isethionova
Potassium 2-hydroxyethanesulfonate
Potassium 2-hydroxyethanesulfonic acid
Potassium 2-hydroxyethanesulphonate
Potassium 2-hydroxyethanesulphonic acid
Potassium isethionate
Potassium isethionic acid
Sodium 2-hydroxyethanesulfonate
Sodium 2-hydroxyethanesulfonic acid
Sodium 2-hydroxyethanesulphonate
Sodium 2-hydroxyethanesulphonic acid
Sodium 2-hydroxyethyl sulfonate
Sodium 2-hydroxyethyl sulfonic acid
Sodium 2-hydroxyethyl sulphonate
Sodium 2-hydroxyethyl sulphonic acid
Sodium b-hydroxyethanesulfonate
Sodium b-hydroxyethanesulfonic acid
Sodium b-hydroxyethanesulphonate
Sodium b-hydroxyethanesulphonic acid
Sodium beta-hydroxyethanesulfonate
Sodium beta-hydroxyethanesulfonic acid
Sodium beta-hydroxyethanesulphonate
Sodium beta-hydroxyethanesulphonic acid
Sodium isethionate
Sodium isethionic acid
Sodium β-hydroxyethanesulfonate
Sodium β-hydroxyethanesulfonic acid
Sodium β-hydroxyethanesulphonate
Sodium β-hydroxyethanesulphonic acid
β-Hydroxyethanesulfonate
β-Hydroxyethanesulfonic acid
β-Hydroxyethanesulphonate
β-Hydroxyethanesulphonic acid

Chemical Formula:

C₂H₆O₄S

Average Molecular Weight:

126.132

Monoisotopic Molecular Weight:

125.99867937

InChI Key:

SUMDYPCJJOFFON-UHFFFAOYSA-N

InChI:

InChI=1S/C2H6O4S/c3-1-2-7(4,5)6/h3H,1-2H2,(H,4,5,6)

CAS number:

107-36-8

IUPAC Name:

2-hydroxyethane-1-sulfonic acid

Traditional IUPAC Name:

sodium isethionate

SMILES:

OCCS(O)(=O)=O

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as sulfonic acids. These are compounds containing the sulfonic acid group, which has the general structure RS(=O)2OH (R is not a hydrogen atom).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Sulfonic acids and derivatives

Sub Class

Sulfonic acids

Direct Parent

Sulfonic acids

Alternative Parents

Substituents

Alkanesulfonic acid
Sulfonyl
Sulfonic acid
Hydrocarbon derivative
Primary alcohol
Organosulfur compound
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

alkanesulfonic acid (CHEBI:1157 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

< 25 °C

Experimental Properties:

Property	Value	Source
Water Solubility:	1000 mg/mL	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	103.0 mg/mL	ALOGPS
logP	-2.2	ALOGPS
logP	-2.9	ChemAxon
logS	-0.09	ALOGPS
pKa (Strongest Acidic)	-1.4	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	22.95 m³·mol^-1	ChemAxon
Polarizability	10.43 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Adenosine triphosphate + Water + Isethionic acid > ADP + Hydrogen ion + Isethionic acid + Phosphate
Adenosine triphosphate + Water + Isethionic acid > ADP + Hydrogen ion + Isethionic acid + Phosphate
FMNH + Isethionic acid + Oxygen > Flavin Mononucleotide + Glycolaldehyde + Hydrogen ion + Water + Sulfite

Pathways:

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-0900000000-f83dca3bb4164fb39fc2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-054k-8900000000-111dba10014f3cc5c403	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056r-9300000000-5cc44eb483ce09d49510	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00e9-6900000000-c1573e4b7aa0acf67018	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0089-9600000000-894c171421adedc823bb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-b8c542a1a77eb7a6a191	View in MoNA

References

References:

Kersten A, Althaus C, Seitz HM, Pfahl HG, Sundmacher R: [Bilateral microsporidial keratitis in an HIV-positive patient with AIDS stage infection] Klin Monatsbl Augenheilkd. 1998 Jun;212(6):476-9. Pubmed: 9715470

Synthesis Reference:

Chen, Zhiwen; Liao, Xiangxu; Qian, Weiqiang; et al. Process for preparation of hydroxyalkanesulfonic acids for plating solutions. Faming Zhuanli Shenqing Gongkai Shuomingshu (1990), 6 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	1157
HMDB ID	HMDB03903
Pubchem Compound ID	7866
Kegg ID	C05123
ChemSpider ID	7578
Wikipedia	Isethionic_acid
BioCyc ID	CPD-3745
EcoCyc ID	CPD-3745

Enzymes

Protein Details

• Alkanesulfonate monooxygenase

General function:: Involved in alkanesulfonate monooxygenase activity
Specific function:: Involved in desulfonation of aliphatic sulfonates. Catalyzes the conversion of pentanesulfonic acid to sulfite and pentaldehyde and is able to desulfonate a wide range of sulfonated substrates including C-2 to C-10 unsubstituted linear alkanesulfonates, substituted ethanesulfonic acids and sulfonated buffers
Gene Name:: ssuD
Locus Tag:: PA3444
Molecular weight:: 41.6 kDa

Reactions

An alkanesufonate (R-CH(2)-SO(3)H) + FMNH(2) + O(2) = an aldehyde (R-CHO) + FMN + sulfite + H(2)O.

Protein Details

• Putative aliphatic sulfonates transport permease protein ssuC

General function:: Involved in transporter activity
Specific function:: Part of a binding-protein-dependent transport system for aliphatic sulfonates. Probably responsible for the translocation of the substrate across the membrane
Gene Name:: ssuC
Locus Tag:: PA3443
Molecular weight:: 28.5 kDa

Protein Details

• Taurine transport system permease protein tauC

General function:: Involved in transporter activity
Specific function:: Part of a binding-protein-dependent transport system for taurine. Probably responsible for the translocation of the substrate across the membrane
Gene Name:: tauC
Locus Tag:: PA3936
Molecular weight:: 29.4 kDa

Protein Details

• Taurine import ATP-binding protein TauB

General function:: Involved in nucleotide binding
Specific function:: Part of the ABC transporter complex TauABC involved in taurine import. Responsible for energy coupling to the transport system
Gene Name:: tauB
Locus Tag:: PA3937
Molecular weight:: 28.8 kDa

Reactions

ATP + H(2)O + taurine(Out) = ADP + phosphate + taurine(In).

Protein Details

• Taurine-binding periplasmic protein

General function:: Involved in transporter activity
Specific function:: Part of a binding-protein-dependent transport system for taurine
Gene Name:: tauA
Locus Tag:: PA3938
Molecular weight:: 35.9 kDa

Protein Details

• Aliphatic sulfonates import ATP-binding protein SsuB

General function:: Involved in nucleotide binding
Specific function:: Part of the ABC transporter complex SsuABC involved in aliphatic sulfonates import. Responsible for energy coupling to the transport system (Probable)
Gene Name:: ssuB
Locus Tag:: PA3442
Molecular weight:: 29.8 kDa

Transporters

Protein Details

• Putative aliphatic sulfonates transport permease protein ssuC

General function:: Involved in transporter activity
Specific function:: Part of a binding-protein-dependent transport system for aliphatic sulfonates. Probably responsible for the translocation of the substrate across the membrane
Gene Name:: ssuC
Locus Tag:: PA3443
Molecular weight:: 28.5 kDa

Protein Details

• Taurine transport system permease protein tauC

General function:: Involved in transporter activity
Specific function:: Part of a binding-protein-dependent transport system for taurine. Probably responsible for the translocation of the substrate across the membrane
Gene Name:: tauC
Locus Tag:: PA3936
Molecular weight:: 29.4 kDa

Protein Details

• Taurine import ATP-binding protein TauB

General function:: Involved in nucleotide binding
Specific function:: Part of the ABC transporter complex TauABC involved in taurine import. Responsible for energy coupling to the transport system
Gene Name:: tauB
Locus Tag:: PA3937
Molecular weight:: 28.8 kDa

Reactions

ATP + H(2)O + taurine(Out) = ADP + phosphate + taurine(In).

Protein Details

• Taurine-binding periplasmic protein

General function:: Involved in transporter activity
Specific function:: Part of a binding-protein-dependent transport system for taurine
Gene Name:: tauA
Locus Tag:: PA3938
Molecular weight:: 35.9 kDa

Protein Details

• Aliphatic sulfonates import ATP-binding protein SsuB

General function:: Involved in nucleotide binding
Specific function:: Part of the ABC transporter complex SsuABC involved in aliphatic sulfonates import. Responsible for energy coupling to the transport system (Probable)
Gene Name:: ssuB
Locus Tag:: PA3442
Molecular weight:: 29.8 kDa

Isethionic acid (PAMDB001641)

Structure for Isethionic acid (PAMDB001641)

Enzymes

Reactions

Reactions

Transporters

Reactions